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A Key West vacation will take you to the furthest of the Florida Keys and southernmost point in the continental U.S. When Spaniards first came here, they called it Key of Bones, or Cayo Hueso, which the English pronounced Key West. Home to laid-back literati and body painted ladies, this independently minded island proclaimed itself The Conch Republic in a mock secession in the 1980s.

The Sun Also Sets

Key West was muse to writers like Ernest Hemingway, John Dos Passos, Robert Frost, and Tennessee Williams. Even Jimmy Buffet wrote novels here. The tradition continues each January at the Key West Literary Seminar.

Hemingway wrote some of his best works here, including A Farewell to Arms and For Whom The Bell Tolls. To locals, he was “Papa,” a regular at the saloons, boxing rings, and fishing piers. Today, descendants of his six-toed cat will greet you at the home where wrote most of his life’s work.

Sky, Sea, and Sand

Key West also offers home tours of another famous resident, bird painter John James Audubon. To glimpse the lush paradise Audubon knew, visit Nancy Forrester’s Secret Garden in Old Town.

A treasure trove of doubloons and pieces-of-eight from a sunken Spanish galleon are displayed at the Mel Fisher Maritime Heritage Museum. You can explore a coral reef without leaving town at the Key West Marine Park, or debark on an excursion to Dry Tortugas National Park. Hemingway fished from Garrison Bight, where charters are available for tarpon, cobia, and shark.

Fantasies Fulfilled

Duval Street is Key West’s Bourbon Street, and local bars are legend. Hemingway characterized Sloppy Joe’s owner in one of his books. He also drank at Captain Tony’s Saloon, mentioned in a Jimmy Buffet song. Another of Buffet’s hits sets the tequila-haze ambiance of his Margaritaville Café.

Each October, Key West travel means Fantasy Fest, a Halloween-meets-Mardi-Gras body-painted bacchanal. Although public nudity is officially taboo, it happens there, so if that’s not your thing, don’t go. If it is, however, the Garden of Eden rooftop bar is clothing-optional year-round. Clothing is also optional poolside at Tea by the Sea, popular with the longstanding local gay scene. Other gay hot spots include Bourbon Bar/Number One Saloon, Aqua, and La Terraza de Marti (“La-Te-Da”).

Key Lime Time

The Key Lime Pie Company dishes out the real deal at two locations. Hemingway once boxed at what is now Ricky’s Blue Heaven restaurant. After dinner, fire up an El Hemingway from the Conch Republic Cigar Factory on “Cigar Alley.”

For an authentic Key West Florida experience, pick up a free copy of Sharon Wells' Walking & Biking Guide to Historic Key West, and head up the back-streets of Bahama Village before it becomes over-gentrified.